ChemInform Abstract: Cycloaddition Reaction of Phosphonyl Nitrile Oxides to Phosphaacetylene and Alkene.

Here, we report the cycloaddition reaction of phosphonyl nitrile oxides and the formation of an unexpected 2:1 cycloaddition product. It provides a direct route to triphosphonyl-substituted dihydroisoxazolyl dihydroisoxazoles and diphosphonyl-substituted dihydroisoxazolyl dihydroisoxazoles with excellent levels of regiocontrol product. Density functional theory studies of the reactions between nitrile oxides and acrylonitrile are used to propose a possible reaction mechanism. (C) 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:95-100, 2009; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20518